About driving around at 40 listening to hip hop ... it depends.
I've been a hip hop head for as long as I can remember, so I definitely plan to. I've become more selective of what I listen to as I've gotten older, and I'm sure in the next 10 years when I turn 40 I'll be even more picky. Even now I have trouble listening to the unedited versions of early Death Row songs, something I never through would happen.
I find myself rotating the same albums around and I think I'll rock them until I'm an old fart - Nas's Illmatic, Cannibal Ox's The Cold Vein, Blackalicious' Nia, Kanye's Graduation, Mos Def's Black on Both Sides, Tribe's Midnight Marauders, Tribe's Low End Theory, Main Source's Breaking Atoms, Rakim's The Book of Life, Jay-Z's Reasonable Doubt, Jay-Z's Blueprint every Roots album ... I'm definitely forgetting some. I know most of them are mid 90s but hey, that's when I feel like the art hit its stride.